Two Days in Chicago, Illinois

Chicago can be a great weekend trip, especially if you live in close proximity to the city like me who is based in Toronto, Canada. The flight is under two hours from Toronto, so when my girl friend and I were looking for a weekend trip to take on the Easter long weekend, Chicago seemed like the perfect place.

From my weekend in Chicago, I put together this two-day itinerary filled with my highlights and recommendations I received from locals and other travelers. Enjoy!

Chicago Cruise

Day One

Wake up early and head down to the Navy Pier by the water. If you’re looking for a place to stay while in Chicago, Hotel Felix is a great eco-friendly boutique hotel located in the River North neighbourhood and close to public transit and other attractions.

Once at Navy Pier, you’ll find several booths along the water selling tickets for their different boat cruises. We picked the architectural boat cruise with Shoreline Sightseeing. The boat cruise is 75 minutes in length and cost from $35.00-$40.00 USD for adults.

This boat cruise takes you down the Chicago River and talks about some of the amazing architecture that makes up the city of Chicago. Even if you aren’t so into building history, seeing the city from the water gives a different perspective and is nice to do (especially if the weather is nice).

Signature Lounge

After your cruise, head to The Signature Lounge which is located on one of the top floors of the John Hancock Centre. When we were in Chicago, we really wanted to go up top the Willis Tower and see the panoramic view, as well as stand on the famous glass floor boxes that hang over the edge of the building. Unfortunately, when we got to the Willis Tower, and stood in line for about 30-45 minutes, we then found out that the wait from the point we were at was upwards of 2-3 hours. To us, with limited time, this simply was not worth it. So we found an alternative.

The Signature Lounge is busy, but on an Easter Sunday, early in the afternoon we had no problem getting in. We ordered one drink each, which were quite expensive (around $15-$18 USD) and enjoyed the view. For the best view, make sure to make a visit to the ladies restroom!

Lincoln Park

After having some fancy and overpriced cocktails at The Signature Lounge, head to Lincoln Park where you can walk around and enjoy the park, the great views of the skyline, or visit the free zoo, and conservatory. Since it was still March when we were there, the park wasn’t green and vibrant yet, and all the zoo animals weren’t out and about, but this can be a great activity, especially if you’re visiting in the warmer months.

After getting some relaxation back at your hotel, get ready to head to the Girl and the Goat for dinner. This restaurant is ranked one of the best restaurants in the city and even the locals recommended it to us. The restaurant is a busy place though; I made our reservation about 1.5 months in advance and was still only able to get a dinner reservation after 10:00pm.

Girl and Goat

Despite having to eat late, it was totally worth the wait and lived up to its hype. The dishes are served in tapa style, which is great as it allows you to try all different dishes. We had the calamari bruschetta, goat empanadas, and the scallops.

Once you finish up dinner, head to Howl at the Moon. This is a lively and fun dueling piano bar that is great for a night out or even just for a few drinks. You’ll be amazed at all the songs these piano players can play on request.

Day Two

The Bean

Wake up bright and early and head to visit Millennium Park and the famous art installation known as Cloud Gate (or The Bean). The Bean is a popular attraction among tourists so the trick to get some good photos and truly enjoy it is to wake up before anyone else does and head to see it. We visited at 8am on Good Friday and managed to get photos with hardly anyone in it (see above).


After a visit to The Bean and Millennium Park, explore Chicago’s food scene by getting yourself on a food tour. We did a food tour of the Wicker Park and Bucktown neighbourhoods with Chicago Food Planet Tours. This tour company also offers other food tours of different neighbourhoods within the city. Another option is the Chicago Pizza Tour, where they will take you to some of the best pizzerias in the city to try some famous Chicago-style deep-dish pizza, and also other variations of pizza.


Either of these tours will take a good chunk of your afternoon, but once you’re done, head to get the ultimate Chicago souvenir, Chicago mix popcorn (a mix of cheddar and caramel popcorn) from the famous Garrett’s Popcorn.

After you have some time to relax, and have all your food digest from the day, head for drinks at Three Dots and a Dash, a retro Polynesian-island bar with a wide selection of rums and fun tiki drinks!

Last but not least, head for dinner at the Frontera Grill, a restaurant by Rick Bayless that is said to have some of the yummiest Mexican food in the city. Unfortunately the night we were supposed to go, I came down with a stomach bug, but I’ve heard nothing but praise about this place from locals and travelers. Don’t forget to make reservations way in advance, as although this joint isn’t as busy as Girl and the Goat, it can still be hard to get into at a normal hour.

Voila! Here is a great way to spend your two days in Chicago, Illinois. Do you have any must-do things in Chicago? Share them in the comments below to help out other travelers!

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1 Comment

  • Reply
    May 2, 2016 at 1:39 pm

    Ah I really want to do a weekend in Chicago! Saving this post for future reference 😉

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